


Valentine's Day

by Dbaw3



Series: Stiles is the Best Girlfriend [2]
Category: Teen Wolf (TV)
Genre: Bottom Stiles Stilinski, Feminization, Genderplay, M/M
Language: English
Status: Completed
Published: 2019-02-21
Updated: 2019-02-21
Packaged: 2019-11-01 19:49:46
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,392
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17873729
Author URL: https://archiveofourown.org/users/Dbaw3/pseuds/Dbaw3
Summary: Stiles decides to give Derek a little something for Valentine's Day. Turns out it's a present for both of them.





	Valentine's Day

The first time it happened, it was just supposed to be a one-time gift for Valentine’s Day. It was also supposed to be something simple.

As everyone from his father to his teachers at school to his best friend liked to tell him, Stiles sometimes got a little carried away.

Not that Derek was complaining.

It started, really, when Derek, after what had felt like hours spent going down on him before fucking him into the mattress, had spooned up behind him. Making a show of pulling something out of his teeth, he told Stiles, “I love your pussy, baby, I just wish you’d shave your muff.”  
Stiles, still a little orgasm-drunk, looked over his shoulder, confused. “You mean my bush?” and gestured down to his groin.

Derek laughed into his neck, and then reached down, tickling Stiles hole which, even though it was super sensitive after all the attention, Stiles pushed back towards him in offering, and hummed in happiness as Derek wiggled his finger inside him again. “Well, that would be nice, too. I bet your clit would look kinda cute without all that hair. But no,” he said, pushing his finger in and out, playing with the cum he’d left there, “I mean you pussy hair. Gets all in my teeth when I go down on you.” 

(Stiles had had a long, sit-down conversation with Derek about the whole feminization thing he had going. Was it just a kink or was it a delusion? He knew Stiles was still a guy, right? That it didn’t make him less gay if he referred to Stiles’ asshole as a pussy and dick as a clit? He didn’t actually WANT Stiles to be a girl, did he? 

After much conversation, most of which was conducted while Derek looked at him as if he were an idiot, Derek convinced him it was about 80% kink and 20% a weird werewolf thing having to do with gendered norms and roles and nurturing from pack females, etc. Yes, he knew Stiles wasn’t a girl, no he didn’t want him to have a sex change, yadda yadda yadda. Stiles had grudgingly also admitted that he was finding most of Derek treating him like his girlfriend hot, so it all seemed to be working out.)

Derek didn’t say anything else about it, but whenever they had oral sex (which was a lot, because Stiles had to admit, he loved sucking cock, and Derek seemed to love eating his ass almost as much), Derek would cough like he was hacking up a hairball or pull bits of hair out of his teeth afterwards with pointed looks.

So, as January was winding down and their first Valentine’s Day together was coming up, Stiles decided he was going to do it. He was going to shave himself. 

Which was an idea easier said than done, and he ended up googling trying to figure out how, exactly, you shave yourself safely from that angle. Which led to him down a rabbit hole of both wonderful and horrifying videos, and then some strangely arousing videos and idea of what Derek might actually like MORE, then suddenly an impulse purchase. Then a rather awkward conversation with Lydia requesting help, which ended up proving how wonderful she was as she didn’t even bat an eye as she showed him how, exactly, to put on his new purchases. (She was so matter of fact, and unsurprised by the revelation of him being the “girl” in his relationship with Derek, Stiles was simultaneously put at ease and borderline insulted.)

Derek had announced ages ago he was taking his “beautiful girl” out for Valentine’s Day. (He’d said it right after a mind-blowing orgasm, so Stiles hadn’t objected too much). And he hadn’t been kidding: he’d told Stiles to dress-up, so Stiles had put on his best slacks and shirt and the one tie he owned, and he still felt under dressed. 

Stiles had debated when to put everything on, and decided what the hell, he’d wear it under his pants. 

It was a weird sensation, especially after shaving, and he had to admit that he liked it, the feel of satin and lace against all that newly sensitized bare skin. But he knew he was even squirmier than usual, and he got more than a few odd looks from Derek throughout the evening.

And Derek. Derek had definitely decided to pull out the stops on being the best boyfriend. Stiles was torn between finding it nice and wanting to punch his sourwolf, every time he held open a door for him or pulled out a chair or ORDERED FOR HIM. Stiles decided, though, at some point, that it was oddly sweet, and he kind of liked it. It was like Derek was taking care of him. It also didn’t hurt that Derek looked even hotter than normal, and when he looked at Stiles like he’d hung the moon, and held his hand in the restaurant like he didn’t care who saw.

He could live with that.

Dinner was nice, though as the evening wore on Stiles got more and more distracted. When they finally got home, Derek wanted to snuggle on the couch and watch something on TV, but Stiles excused himself to the bathroom. 

Which is how Stiles found himself standing in his own bathroom, wearing only panties, garters and stockings, and feeling a little ridiculous. 

Should he go out there just like this and try to act sexy? The problem was, he was TERRIBLE at acting sexy. Derek seemed to think he was sexy without trying, but years of awkward teenhood were barely behind him, so it kind of weighted on his mind. Also, what had seemed hot when he found the site of men’s lingerie, now looked strange in the mirror.

Whatever, Stiles thought. He was here, Derek was waiting. The worst he could do was laugh. He’d faced scarier things in Beacon Hills.

He tried to convince himself of this, and just opened the door and stepped out into the livingroom before he could talk himself out of it.

Derek didn’t laugh.

At first Derek didn’t do or say anything, he just stared. He stared so long, Stiles thought about dashing back into the bathroom and hiding in there until he was 60. But then his mouth started moving and finally words emerged.

“Stiles,” he gasped. “Baby. You’re gorgeous.”

Stiles felt like collapsing, he was so relieved, but tried striking a pose instead. “Really?” he asked in what he hoped was a coquetish voice. “You like it?”

Derek palmed the obvious bulge in his own pants. “Babygirl, come over here and let me show you how much I like it,” he said intently.

Stiles felt a slight thrill go through him at the new endearment–one that probably shouldn’t have surprised him, considering other things Derek had said to him recently and the fact that he was standing there in lingerie–and moved quickly, but still slightly unsure.

Derek reached for him as soon as he was in range. “There’s my sweet girl,” Derek murmured, and ran his palms all over Stiles making him groan: around his hips, down his legs, and finally up around his satin-covered dick.

“Oh, baby, you’re already so wet,” Derek cooed, even as his thumb rubbed at Stiles’ cockhead through his panties. “Your clit is leaking everywhere.”

It was true: Stiles was practically a fountain now, precome pouring out of him and soaking through the material trapping his dick. Then Derek did the one thing Stiles thought he would never do, and nearly gave him a heart attack: he licked a stripe up his dick from crotch of the panties all the way up the front.

“God, Derek,” Stiles cried out, grabbing his head with both hands.

Derek moaned against the head of Stiles’ dick, and grinned up at him. “You love it when I lick your little clitty, don’t you?”

“Derek,” Stiles moaned again.

“Come on, sweetie,” Derek said, just nuzzling him. “Say it. Say you love it when I play with your clit.”

“Fuck, Derek,” Stiles gasped. “Fuck, play with my clitty, please.”

Derek moaned again, and nipped at the head of his clit, causing Stiles to spasm so hard he thought he was having a seizure. 

“My beautiful girl,” Derek said, pulling away, but still grasping at Stiles’ hips. “Baby, I need your pussy so bad, turn around.”

Stiles did in a daze, though he whimpered at the thought of giving up the unusual attention to his dick.

He needn’t have worried, though: While Derek gasped at the sight of the lacy thong in his crack, his hand moving back to frame Stiles’ crotch, his thumb rubbing against Stiles’ cockhead. Then he moved the thong out of the way with his other hand, which was followed by another gasp and moan and then he bit Stiles’ left ass cheek. Stiles yelped.

“Baby, you shaved?” Derek said, so close Stiles could feel his hot breath on his hole, and it made him twitch. “I can’t believe you shaved your pussy for me. You’ve got to let me watch next time.”

Stiles, who hadn’t really thought about this as anything more than a one-time present for his boyfriend, was so lost in the sensations he didn’t say anything.

Then Derek leaned forward and began to eat him out. God, it felt so amazing. Derek tongue in his pussy always made him wild, but with all the hair removed, it was like every sensation was heightened. Stiles was delirious, but soon enough, with Derek voracious making love to his pussy and touching him in front, Stiles found himself reach down and taking Derek’s hand, then asking what he thought he’d never hear himself ask.

“Baby,” Stiles moaned, half-sobbing, as he pulled Derek’s hand away. “Stop, it’s too much.”

Derek instantly pulled back, and turned him around to look at him with concern. “What, Stiles? Did I hurt you?”

“No,” he said, and he really was close to crying, but desperate for more. “I need you to keep eating me. But you have to stop touching my clit.”

Derek’s eyes lit up, and Stiles realized it was the first time he’d called it his clit without any prompting. Even in the middle of all this, it filled him with such tenderness to see how much it meant to Derek, he vowed to do it more right then.

“So, you don’t want me playing with your clit anymore, baby?” Derek asked deliberately, and ran his thumb against it again. Stiles shivered at the over stimulation and nodded. 

Then he looked down at Derek and deliberately said, “No, please: don’t touch my clit. Just keep eating my pussy.”

Derek growled then, and Stiles thought he might have lost time, as the next thing he knew his panties were gone, and he was on his back on the couch, rolled up onto his shoulder and his legs held out almost in splits as Derek dived back into his cunt.  

When the first orgasm hit Stiles, he thought his clit was going to explode, it felt so strong.

The second one, which happened only five minutes later was much stronger, another of those “pussy orgasms” Derek sometimes gave him, starting somewhere deep inside him, and his now-soft dick barely giving a twitch, even as he felt the rest of him shuddering in pleasure.

Derek finally raised his head, and lowered Stiles’ legs. His face was wet and his eyes were glassy, even as he muttered “Gotta fuck that pussy.”

Stiles was happy to be man-handled (wolf-handled?) back onto his front, before Derek pushed inside of him. Now that his mind wasn’t clouded with his own need to orgasm, he was almost able to enjoy this more, the feeling of Derek inside of him. And even with this, he could tell the difference from him shaving, it was almost as if he could feel more of Derek’s cock stretching his hole open.

“Fuck, love your bare pussy,” Derek said into his neck. “Gotta fuck it in our bed.”

With that, he picked Stiles up, still impaled on his cock. Stiles squealed in delight: he loved Derek showing his strength so casually, and as he walked them both so effortlessly to the bedroom, his hands under Stiles’ thighs, just where the tops of his stockings. Stiles loved the feeling of Derek’s cock, still pumping deeper inside of him with each step, and he was almost disappointed when they got to the bed, and Derek lowered him down gently to it.

Not for long, though, as Derek, never disconnecting them, climbed on top and started fucking into him in earnest, even while detaching each of the garters, and moving Stiles’ stockings down his leg, as he felt them up.

“Fuck, love that you’d do this for me, babygirl,” he growled in Stiles’ ear. “Love these stockings and you so bare. Love the panties and the garters, and I fucking love you shaved your pussy for me.”

Stiles mewled, and pushed his knees up, giving more of his pussy to his boyfriend. He started to feel another pussygasm heading his way.

“Fucking love everything you do for me, baby,” Derek continued muttering, even as he fucked into Stiles harder and harder. “Fuck, love you, fuck!”

Stiles didn’t know if they came at the same time, because the stars exploded in his pussy and his head too bright to tell.

They lay there, tangled up and panting for several minutes, both trying to get their breath. It took a while for Stiles’ head to clear enough to realize that he was now lying in his garter belt, one stocking completely off and gone…somewhere. The other dangled somewhere around his ankle.

Stiles couldn’t help the giggle at the thought of how he must look. “Well, this is sexy,” he said into the pillow, and smiled harder as Derek nuzzled the back of his neck.

“You’re the sexiest girl in the world,” Derek said. “I gotta buy you more panties.”

Stiles smiled at that and didn’t argue, feeling too content with Derek’s cock still soaking inside his pussy. “That works out,” he said instead. “Cause you’re the sexiest guy.”

Stiles, for once, let himself be happy that he had such a good boyfriend to be a good girlfriend for.

**Author's Note:**

> Originally posted to Tumblr.


End file.
